An HTS substrate for sEH
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PHOME

Item No. 10009134

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-phenyl-cyano(6-methoxy-2-naphthalenyl)methyl ester-2-oxiraneacetic acid
CAS Number
1028430-42-3
Molecular Formula
C23H19NO4
Formula Weight
373.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/ml
λmax
234 nm
SMILES
COC1=CC=C2C=C(C(OC(CC3OC3C4=CC=CC=C4)=O)C#N)C=CC2=C1
InChi Code
InChI=1S/C23H19NO4/c1-26-19-10-9-16-11-18(8-7-17(16)12-19)21(14-24)27-22(25)13-20-23(28-20)15-5-3-2-4-6-15/h2-12,20-21,23H,13H2,1H3
InChi Key
NZOVBSWOWQLAJG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $43

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    5 mg

    $204

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    10 mg

    $344

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    50 mg

    $1,073

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    Product Description

    EpETrE metabolites of arachidonic acid such as 11(12-EpETrE and 14(15)-EpETrE have been identified as endothelium derived hyperpolarizing factors with vasodilator activity.1 Soluble epoxide hydrolase (sEH) catalyzes the conversion of EpETrEs to the corresponding DiHETrEs thereby diminishing their activity.2 Inhibitors of sEH may therefore have clinical utility for treating hypertension and systemic inflammation.3,4 PHOME is a fluorogenic substrate for human sEH which displays good aqueous stability and solubility making it ideal for high throughput screening (HTS) programs. Hydrolysis of the substrate yields a highly fluorescent product that can be monitored at excitation and emission wavelengths of 330 and 465 nm, respectively. This fluorescent assay has a sensitivity that is 100 times greater than previously used spectrophotometric assays.5 NOTE: This substrate should only be used with the pure EH. If this substrate is used with crude enzyme preparations it is critical that all esterase activity is removed or inhibited, such as with organophosphate or a trifluoroketone inhibitor, and that glutathione is depleted and/or glutathione S-transferase is inhibited.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fleming, I. Cytochrome P450 epoxygenases as EDHF synthase(s). Pharmacol. Res. 49(6), 525-533 (2004).

    2. Morisseau, C., Goodrow, M.H., Newman, J.W., et al. Structural refinement of inhibitors of urea-based soluble epoxide hydrolases. Biochem. Pharmacol. 63(9), 1599-1608 (2002).

    3. Imig, J.D., Zhao, X., Zaharis, C.Z., et al. An orally active epoxide hydrolase inhibitor lowers blood pressure and provides renal protection in salt-sensitive hypertension. Hypertension 46(2), 975-981 (2005).

    4. Schmelzer, K.R., Kubala, L., Newman, J.W., et al. Soluble epoxide hydrolase is a therapeutic target for acute inflammation. Proc. Natl. Acad. Sci. USA 102(28), 9772-9777 (2005).

    5. Wolf, N.M., Morisseau, C., Jones, P.D., et al. Development of a high-throughput screen for soluble epoxide hydrolase inhibition. Anal. Biochem. 355, 71-80 (2006).

    Product Citations

    Van Anh, T.T., Mostafa, A., Rao, Z., et al. From Vietnamese plants to a biflavonoid that relieves inflammation by triggering the lipid mediator class switch to resolution. Acta Pharm. Sin. B. 11(6), 1629-1647 (2021).